Mar 20, 2024; Portland, Oregon, USA; LA Clippers guard James Harden (1) dribbles past Portland Trail Blazers guard Anfernee Simons (1) as Clippers center Daniel Theis (10) watches in the second quarter at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images Jaime Valdez-Imagn Images

Bucks Considering Trade for $100 Million Guard on East Rival: Report

Originally posted on Milwaukee Bucks on SI
By Nelson Espinal | Last updated Aug 25, 2025 11:30 AM ET

The Milwaukee Bucks may end up trading for guard Anfernee Simons ahead of the start of NBA training camps.

A deal for Simons would land the Bucks a starting-caliber guard — addressing the weakest point on their roster.

Milwaukee waived Damian Lillard to create enough cap space for the signing of Turner. Lillard was going to miss the upcoming season with a torn Achilles, making the move about current availability rather than long-term planning.

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Currently, a combination of Kevin Porter Jr. and Cole Anthony is expected to start, and while there is room for growth with both players, neither inspires confidence for the upcoming season compared to other backcourts around the league.

This is where Simons enters the picture — he is a promising young guard who can space the floor, playmake for others, and is only 26 years old, giving him plenty of upside that he has not tapped into.

According to reporting from Sam Amico of Hoops Wire, Simons is still being shopped by the Boston Celtics, a team that is looking to shed salary from their books.

“Sources said the Bucks could be another team that will make a run at Simons before training camp," Amico wrote in a story.

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Simons averaged 19.3 points last season while shooting 42.6 percent from the floor and 36.3% from deep.

These are numbers playing with the Portland Trail Blazers, a team that has lacked playoff-caliber talent.

Simons Could Thrive in Milwaukee

With the Bucks, Simons would have the best supporting cast of his career, helping him achieve his full potential.

The Bucks boast one of the best front courts in the NBA. Myles Turner and Giannis Antetokounmpo provide defensive and offensive flexibility, and both cover up each other's weaknesses.

Turner is a premier stretch five who can space the court for dribble penetration, though he lacks elite rebounding for a center. On the other hand, Antetokounmpo struggles to shoot from the perimeter, but rebounds at an elite level and can attack the basket off the dribble.

The combination of Turner and Antetokounmpo gives the Bucks a leg up in the Eastern Conference, but as strong as their big man positions are, there are plenty of questions left at guard.